WO2019146506A1 - Composé, composition liquide, feuille d'enregistrement par transfert thermique, toner, composition de réserve pour filtre coloré et filtre coloré - Google Patents

Composé, composition liquide, feuille d'enregistrement par transfert thermique, toner, composition de réserve pour filtre coloré et filtre coloré Download PDF

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Publication number
WO2019146506A1
WO2019146506A1 PCT/JP2019/001367 JP2019001367W WO2019146506A1 WO 2019146506 A1 WO2019146506 A1 WO 2019146506A1 JP 2019001367 W JP2019001367 W JP 2019001367W WO 2019146506 A1 WO2019146506 A1 WO 2019146506A1
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group
compound
carbon atoms
substituent
unsubstituted
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PCT/JP2019/001367
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English (en)
Japanese (ja)
Inventor
城田　衣
太一 新藤
愛 早川
三東　剛
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キヤノン株式会社
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Publication of WO2019146506A1 publication Critical patent/WO2019146506A1/fr
Priority to US16/930,463 priority Critical patent/US11021436B2/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/62—Quaternary ammonium compounds
    • C07C211/64—Quaternary ammonium compounds having quaternised nitrogen atoms bound to carbon atoms of six-membered aromatic rings
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/382—Contact thermal transfer or sublimation processes
    • B41M5/38235—Contact thermal transfer or sublimation processes characterised by transferable colour-forming materials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/382—Contact thermal transfer or sublimation processes
    • B41M5/385—Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/382—Contact thermal transfer or sublimation processes
    • B41M5/385—Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
    • B41M5/3854—Dyes containing one or more acyclic carbon-to-carbon double bonds, e.g., di- or tri-cyanovinyl, methine
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/382—Contact thermal transfer or sublimation processes
    • B41M5/385—Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
    • B41M5/39—Dyes containing one or more carbon-to-nitrogen double bonds, e.g. azomethine
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/382—Contact thermal transfer or sublimation processes
    • B41M5/392—Additives, other than colour forming substances, dyes or pigments, e.g. sensitisers, transfer promoting agents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/382—Contact thermal transfer or sublimation processes
    • B41M5/392—Additives, other than colour forming substances, dyes or pigments, e.g. sensitisers, transfer promoting agents
    • B41M5/395—Macromolecular additives, e.g. binders
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
    • C07C251/30—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having nitrogen atoms of imino groups quaternised
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B53/00—Quinone imides
    • C09B53/02—Indamines; Indophenols
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B55/00—Azomethine dyes
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/201—Filters in the form of arrays
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/09—Colouring agents for toner particles
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/097—Plasticisers; Charge controlling agents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M2205/00—Printing methods or features related to printing methods; Location or type of the layers
    • B41M2205/02—Dye diffusion thermal transfer printing (D2T2)
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M2205/00—Printing methods or features related to printing methods; Location or type of the layers
    • B41M2205/30—Thermal donors, e.g. thermal ribbons
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M2205/00—Printing methods or features related to printing methods; Location or type of the layers
    • B41M2205/40—Cover layers; Layers separated from substrate by imaging layer; Protective layers; Layers applied before imaging
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/40—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used characterised by the base backcoat, intermediate, or covering layers, e.g. for thermal transfer dye-donor or dye-receiver sheets; Heat, radiation filtering or absorbing means or layers; combined with other image registration layers or compositions; Special originals for reproduction by thermography
    • B41M5/42—Intermediate, backcoat, or covering layers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus

Definitions

  • the present invention relates to a compound, a liquid composition, a sheet for thermal transfer recording, a toner, a resist composition for a color filter, and a color filter.
  • the thermal transfer recording method is excellent as a method that can be printed easily regardless of the surrounding environment because printing can be performed by a dry process, the apparatus can be miniaturized, and the portability of the printer is excellent.
  • the thermal transfer recording methods in the thermal sublimation transfer method, the dye is transferred, diffused, and fixed on the image receiving sheet in the form of a single molecule by thermal energy to form an image.
  • the heat-sensitive sublimation transfer system has attracted attention in recent years because it can express color tone and gradation close to silver salt photographs, but since the dye is diffused as a single molecule in the substrate, there is a problem in light resistance.
  • Patent Document 1 discloses a thermal transfer sheet capable of improving the light resistance of a dye after thermal transfer by containing a discoloration inhibitor. Further, in Patent Document 2, as a protective layer transfer sheet capable of imparting high light resistance to an image formed on a transfer target, at least copolymerization of styrene and an ultraviolet absorbing monomer is carried out on the surface layer. A protective layer transfer sheet comprising the copolymer is disclosed.
  • Patent Document 3 discloses an example using an azomethine dye as a toner colorant.
  • dyes of high chroma have lower light resistance than conventional pigments, and thus the problem is that the storability of colored materials is poor, and means for achieving both light fastness and high chroma Was required.
  • An object of the present invention is to provide a compound which improves the light resistance of a coloring matter. Another object of the present invention is to provide a liquid composition containing the compound. Another object of the present invention is to provide a heat-sensitive transfer recording sheet excellent in light resistance, a toner and a resist composition for a color filter by using the compound.
  • the present invention relates to a compound represented by the following formula (1) or (2).
  • R 1 and R 2 are each independently Represents an unsubstituted alkyl group having 1 to 8 carbon atoms
  • R 3 and R 4 are each independently Hydrogen atom, An unsubstituted alkyl group having 1 to 8 carbon atoms or an alkyl group having a substituent
  • R 3 and R 4 combine to form a nitrogen-containing heterocyclic ring
  • R 5 and R 6 are each independently Hydrogen atom, An unsubstituted alkyl group having 1 to 8 carbon atoms or an alkyl group having a substituent
  • the present invention is a liquid composition
  • a liquid composition comprising a medium, and a compound and a coloring material which are present in a state of being dissolved or dispersed in the medium, wherein the compound is the above-mentioned compound. is there.
  • the present invention is a thermal transfer recording sheet comprising a substrate and a color material layer formed on the substrate, wherein the color material layer contains the above-mentioned compound. Sheet.
  • the present invention also includes a substrate, and a colorant layer and a protective layer formed on the substrate, wherein the colorant layer and the protective layer are formed surface-sequentially.
  • a sheet, The thermal transfer recording sheet is characterized in that the protective layer contains the above-mentioned compound.
  • the present invention is a resist composition for toner or color filter characterized by containing a binder resin, a colorant and the above-mentioned compound. Furthermore, the present invention is a color filter characterized by having a resist layer containing the above-mentioned compound.
  • the present invention it is possible to provide a compound that improves the light resistance of a colored material. Moreover, the liquid composition excellent in the storage property at the time of storage containing this compound can be provided. Further, according to the present invention, it is possible to provide a thermal transfer recording sheet and a toner that provide recorded matter excellent in light resistance. Further, according to the present invention, it is possible to provide a resist composition for a color filter which provides a color filter excellent in light resistance. Furthermore, a color filter excellent in light resistance can be provided.
  • FIG. 1 is a schematic view showing an example of a thermal transfer recording sheet according to the present invention.
  • FIG. 1 is a schematic view showing an example of a thermal transfer recording sheet according to the present invention.
  • R 1 and R 2 are each independently Represents an unsubstituted alkyl group having 1 to 8 carbon atoms
  • R 3 and R 4 are each independently Hydrogen atom, An unsubstituted alkyl group having 1 to 8 carbon atoms or an alkyl group having a substituent
  • R 3 and R 4 combine to form a nitrogen-containing heterocyclic ring
  • R 5 and R 6 are each independently Hydrogen atom, An unsubstituted alkyl group having 1 to 8 carbon atoms or an alkyl group having a substituent
  • the C 1 to C 8 unsubstituted alkyl group of R 1 and R 2 is not particularly limited, and examples thereof include the following. Methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, sec-butyl group, tert-butyl group, iso-butyl group, octyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, methylcyclohexyl Group, cyclohexylmethyl group, 2-ethylpropyl group, 2-ethylhexyl group and the like.
  • the case of the above-mentioned alkyl group having 1 to 4 carbon atoms is preferable, and in particular, the case of a methyl group is more preferable.
  • examples of the unsubstituted alkyl group having 1 to 8 carbon atoms of R 3 and R 4 are not particularly limited, and examples thereof include the following. Methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, sec-butyl group, tert-butyl group, iso-butyl group, octyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, methylcyclohexyl Group, cyclohexylmethyl group, 2-ethylpropyl group, 2-ethylhexyl group and the like.
  • Examples of the substituent of the alkyl group having a substituent at R 3 and R 4 can be exemplified cyano group, an alkoxy group.
  • the unsubstituted alkenyl group as R 3 to R 6 in the formula (1) is not particularly limited, and a vinyl group, propenyl group, butenyl group, pentenyl group, hexenyl group, heptenyl group, octanyl group, etc. Can be mentioned.
  • a substituent of the alkenyl group which has a substituent an alkyl group, a cyano group, an alkoxy group, etc. are mentioned.
  • the unsubstituted aralkyl group having 7 to 12 carbon atoms as R 3 to R 6 is not particularly limited, and examples thereof include a benzyl group and naphthyl.
  • a substituent of the aralkyl group which has a substituent an alkyl group, a cyano group, and an alkoxy group can be mentioned.
  • the unsubstituted aryl group having 6 to 12 carbon atoms in R 3 to R 6 is not particularly limited, but is a phenyl group or a naphthyl group.
  • an alkyl group, a cyano group, and an alkoxy group can be mentioned, for example.
  • R 3 and R 4 and / or R 5 and R 6 may combine to form a nitrogen-containing heterocyclic ring. That is, a cyclic structure containing R 3 and R 4 and a nitrogen atom (N atom), or a cyclic structure containing R 5 and R 6 and a nitrogen atom (N atom) may be formed.
  • the cyclic structure is not particularly limited, but, for example, a 5-membered ring which may have a substituent, a 6-membered ring which may have a substituent, and a substituent A good 7-membered ring can be mentioned. More specifically, the following can be mentioned as this cyclic structure.
  • a 5-membered ring for example, a pyrrolidine ring
  • a 6-membered ring for example, a piperidine ring, a morpholine ring, and a piperazine ring
  • a 7-membered ring for example, an azepane ring
  • alkyl groups such as a methyl group and an ethyl group
  • R 3 to R 6 are preferably an ethyl group, an n-butyl group, a 2-ethylhexyl group and the like from the viewpoint of becoming a compound for improving the light resistance of the colored material.
  • X - is an anion which can be shown, but the present invention is not particularly limited.
  • the anion include the following. Fluorine ion, chlorine ion, bromine ion, iodine ion, perchlorate ion (ClO 4 -), nitrate ion, methanesulfonate ion, benzenesulfonate ion, p- toluenesulfonate ion, p- trifluoromethyl sulfonate ions, 2,3,4,5,6-pentafluoro-benzenesulfonic acid ion, methyl sulfate ion, ethyl sulfate ion, propyl sulfate, tetrafluoroborate ion (BF 4 -), tetraphenylborate ion, hexafluoro Phosphate ion (PF 6
  • the compounds represented by the formula (1) and the formula (2) may be considered to have the presence of structural isomers such as cis-trans, but these structural isomers are within the scope of the present invention.
  • R 1 to R 6 in each compound in the above reaction formula are as defined above.
  • the compound represented by the formula (1) includes an isomer to which a cationic species has been transferred, but all are within the scope of the present invention, and the compound represented by the formula (1) is a mixture thereof. It may be.
  • the compound represented by the formula (1) can be produced, for example, through an oxidation step by silver salt oxidation or electrolytic oxidation reaction through a condensation step of condensing the diamino compound compound (A) and the halide (B) it can.
  • the condensation step is It may be produced by carrying out multiple steps of halides.
  • the condensation step for obtaining the condensation compound (C), which is an intermediate for obtaining the compounds represented by Formula (1) and Formula (2), will be described.
  • the condensation compound (C) can be produced by condensing the diamino compound (A) and the halide (B). Preferred examples of the diamino compound (A) are shown in the following (A-1) to (A-11), but the present invention is not limited thereto.
  • halide (B) Preferred examples of the halide (B) are shown in the following (B-1) to (B-13), but the present invention is not limited thereto.
  • the halide describes a bromo compound, there is no problem with either a chloro compound or an iodine compound.
  • the condensation reaction can be carried out without a solvent, but is preferably carried out in the presence of a solvent.
  • the solvent is not particularly limited as long as it does not inhibit the reaction, and, for example, the following may be used alone or in combination of two or more depending on the solubility of the substrate.
  • This step is usually carried out in a temperature range of 0 to 220 ° C. and is usually completed within 24 hours.
  • the reaction temperature in the condensation step is preferably in the range of 5 to 180 ° C., and more preferably 10 to 120 ° C. If the temperature is lower than 0 ° C., the reaction proceeds significantly, and if the temperature is higher than 220 ° C., decomposition of the compound may occur, which is not preferable.
  • the amount of the reaction solvent used is preferably 0.1 to 1000% by mass, more preferably 1.0 to 150% by mass, based on the diamino compound (A).
  • the condensing agent used in this step is not particularly limited, and examples thereof include Ullmann condensation reaction using a copper compound and Buchwald-Hartwig reaction using a palladium compound.
  • the amount of the condensing agent to be used is preferably 0.0005 to 0.1 mol, more preferably 0.001 to 0.05 mol, per 1 mol of the diamino compound (A).
  • a cocatalyst of a condensing agent can be used in this step.
  • the promoter for the Ullmann condensation reaction is not particularly limited as long as it is a known one classified as an Ullmann condensation reaction.
  • amine compounds such as 2,2′-bipyridyl and 1,10-phenanthroline are preferable because they are inexpensive and easy to use.
  • the co-catalyst for the Buchwald-Hartwig reaction is not particularly limited as long as it is a known one classified as the Buchwald-Hartwig reaction.
  • phosphorus compounds such as 2- (di-tert-dibutylphosphino) biphenyl are preferred.
  • a base in order to accelerate the reaction, it is preferable to use a base.
  • the base include the following. Pyridine, 2-methylpyridine, piperidine, diethylamine, diisopropylamine, triethylamine, phenylethylamine, isopropylethylamine, methylaniline, 1,4-diazabicyclo [2.2.2] octane (DABCO), tetrabutylammonium hydroxide, 1,
  • Organic bases such as 8-diazabicyclo [5.4.0] undecene (DBU); organic metals such as n-butyllithium, tert-butylmagnesium chloride; sodium borohydride, metal sodium, potassium hydride, calcium oxide, carbonate
  • Inorganic bases such as potassium; potassium tert-butoxide, sodium tert-butoxide, and metal alkoxides such as sodium ethoxide.
  • metal alkoxides such as potassium carbonate, potassium tert-butoxide, sodium tert-butoxide and sodium ethoxide are preferable, and particularly, potassium tert-butoxide and sodium tert-butoxide are more preferable.
  • the amount of the base used is preferably 0.1 to 20% by mass, more preferably 0.2 to 5% by mass, with respect to the diamino compound (A).
  • weakly basic salts such as potassium acetate can also be used as in the case of the above-mentioned bases.
  • condensation compound (C) After completion of the condensation reaction, post-treatment is carried out according to the post-treatment method generally used in organic synthesis reactions, and if necessary, purification such as liquid separation operation, recrystallization, reprecipitation, column chromatography and the like is carried out. By doing so, the compound of the present invention represented by condensation compound (C) can be obtained with high purity.
  • the compound represented by Formula (1) or (2) can be manufactured by performing silver salt oxidation or electrolytic oxidation reaction to the condensation compound (C) obtained at the condensation process.
  • a compound represented by the formula (1) is produced by using 1 mol of silver salt per 1 mol of condensation compound (C), and a compound represented by the formula (1) is produced, and 2 mol of 1 mol of condensation compound (C) If a silver salt is used, the compound represented by Formula (2) will be manufactured.
  • Examples of preferable compounds as the compound of the present invention represented by the formula (1) are shown in the following compounds (1-1) to (1-15), but the present invention is not limited thereto.
  • Tf represents a trifluoromethanesulfonyl group (CF 3 SO 2- ).
  • At least one of the above compounds (1-3), (1-4), (1-5), (1-6), (1-8), (1-10), and (1-12) It is preferable to use it from a viewpoint of improving the light resistance of a coloring matter.
  • examples of preferable compounds as the compound of the present invention represented by the formula (2) are shown in the following compounds (2-1) to (2-15), but the present invention is not limited thereto.
  • Tf represents a trifluoromethanesulfonyl group.
  • At least one of the above compounds (2-3), (2-4), (2-5), (2-6), (2-8), (2-10), and (2-12) It is preferable to use it from a viewpoint of improving the light resistance of a coloring matter. In particular, it is preferable to use at least one of (2-3), (2-8) and (2-12).
  • 1 type When using the compound represented by the said Formula (1) and Formula (2), 1 type may each be used independently, and 2 or more types may be used together according to a use.
  • it can use as a liquid composition containing the medium which melt
  • the inclusion of the colorant in the liquid composition is not essential.
  • the coloring agent When the coloring agent is not contained, the effect of the present invention can be obtained by bringing the coloring agent applied on the substrate and the liquid composition close to each other on the substrate.
  • the compound of the present invention can improve the light resistance of the colorant by, for example, being in close proximity to the colorant contained in the recording paper and the color filter.
  • the colorant is not particularly limited, but in the case of a dye, the effects of the present invention are more exhibited.
  • an oil-based dye generally called a disperse dye or a sublimation dye can be suitably used.
  • the effects of the present invention are most exhibited when used in combination with anthraquinone dyes having high chroma, methine dyes, azomethine dyes, and triphenylmethane dyes.
  • the amount of the compound of the present invention to be used is not particularly limited, but it may be used in the range of 0.1 parts by mass to 100 parts by mass with respect to 100 parts by mass of the colorant (total mass parts of the colorants). it can.
  • the range of 0.5 parts by mass to 50 parts by mass is preferable, and in particular, the range of 1.0 parts by mass to 30 parts by mass is more preferable.
  • the compounds represented by the formulas (1) and (2) of the present invention have the following features. That is, it has near infrared absorption with a maximum absorption wavelength of 900 nm or more and 1,400 nm or less. Furthermore, since the absorption in the visible range is small, there is almost no possibility of causing a change in color tone or fading of the colorant.
  • a liquid composition containing the compound represented by the above formula (1) or (2), a sheet for thermal transfer recording, a toner and a resist composition for a color filter will be described in order.
  • the liquid composition of the present invention can be obtained by dispersing or dissolving at least a medium and the compound represented by the formula (1) or (2) in the medium. Furthermore, the liquid composition is appropriately selected according to the use to be used. For example, additives such as a coloring agent, an emulsifying agent, and a resin may be included as long as the characteristics in various applications are not impaired.
  • medium means water or an organic solvent.
  • organic solvent used as the medium
  • the type of the organic solvent is selected according to the application of the liquid medium and is not particularly limited.
  • an organic solvent the following are mentioned, for example.
  • Alcohols such as methanol, ethanol, denatured ethanol, isopropanol, n-butanol, isobutanol, tert-butanol, sec-butanol, 2-methyl-2-butanol, 3-pentanol, octanol, benzyl alcohol, cyclohexanol; methyl Glycols such as cellosolve, ethyl cellosolve, diethylene glycol and diethylene glycol monobutyl ether; Ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; esters such as ethyl acetate, butyl acetate, ethyl propionate and cellosolve acetate; hexane, octane, petroleum ether Aliphatic hydrocarbons such as cyclohexane; aromatic hydrocarbons such as benzene, toluene, and xy
  • a polymerizable monomer can also be used as an organic solvent.
  • the polymerizable monomer includes an addition polymerizable monomer or a condensation polymerizable monomer, and is preferably an addition polymerizable monomer. Specific examples of the polymerizable monomer include the following.
  • Styrene monomers such as styrene, ⁇ -methylstyrene, ⁇ -ethylstyrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, o-ethylstyrene, m-ethylstyrene, p-ethylstyrene, etc .; acrylic Methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, octyl acrylate, dodecyl acrylate, stearyl acrylate, behenyl acrylate, 2-ethylhexyl acrylate, dimethylaminoethyl acrylate, diethylaminoethyl acrylate, acrylonitrile, Acrylate monomers such as acrylic acid amide; methyl methacrylate, ethyl methacrylate, prop
  • colorant in the liquid composition of the present invention, known colorants may be used in combination as long as the solubility or dispersibility of the compound represented by the formula (1) or (2) of the present invention in the medium is not inhibited.
  • the colorant is not particularly limited, but an oil-based dye called a disperse dye or a sublimation dye can be suitably used.
  • the effects of the present invention are most exhibited when used in combination with a highly saturated methine dye, azomethine dye, triphenylmethane dye or the like.
  • the use amount of the compound of the present invention is not particularly limited, but it may be used in the range of 0.1 parts by mass to 100 parts by mass with respect to 100 parts by mass of the colorant (total mass part of the colorant). it can.
  • the range of 0.5 parts by mass to 50 parts by mass is preferable, and in particular, the range of 1.0 parts by mass to 30 parts by mass is more preferable.
  • an emulsifier When water is used as the medium of the liquid medium according to the present invention, an emulsifier may be added as necessary to obtain good dispersion stability of the colorant.
  • an emulsifier although it does not specifically limit, a cationic surfactant, an anionic surfactant, and a nonionic surfactant are mentioned.
  • the cationic surfactant include the following. Dodecyl ammonium chloride, dodecyl ammonium bromide, dodecyl trimethyl ammonium bromide, dodecyl pyridinium chloride, dodecyl pyridinium bromide, hexadecyl trimethyl ammonium bromide and the like.
  • anionic surfactant examples include fatty acid soaps such as sodium stearate and sodium dodecanoate, sodium dodecyl sulfate, sodium dodecyl benzene sulfate and sodium lauryl sulfate.
  • nonionic surfactant examples include the following. Dodecyl polyoxyethylene ether, hexadecyl polyoxyethylene ether, nonylphenyl polyoxyethylene ether, lauryl polyoxyethylene ether, sorbitan monooleate polyoxyethylene ether, monodecanoyl sucrose and the like.
  • the liquid medium of the present invention may further contain a resin.
  • the type of resin is determined according to the purpose and application of the liquid medium, and is not particularly limited. For example, the following may be mentioned. Styrene polymers, acrylic acid polymers, methacrylic acid polymers, polyester resins, polyvinyl ether resins, polyvinyl methyl ether resins, polyvinyl alcohol resins, polyvinyl butyral resins, polyurethane resins, polypeptide resins and the like. One of these resins may be used alone, or two or more of these resins may be used in combination as needed.
  • the dispersing machine is not particularly limited, but media-type dispersing machines such as a rotary shear type homogenizer, a ball mill, a sand mill, an attritor, etc., and a high pressure counter collision type dispersing machine can be used.
  • media-type dispersing machines such as a rotary shear type homogenizer, a ball mill, a sand mill, an attritor, etc., and a high pressure counter collision type dispersing machine can be used.
  • media-type dispersing machines such as a rotary shear type homogenizer, a ball mill, a sand mill, an attritor, etc.
  • a high pressure counter collision type dispersing machine can be used.
  • the liquid composition of the present invention contains the compound represented by the formula (1) or (2), it has a feature of improving the light resistance of the colored material.
  • the thermal transfer recording sheet according to the present invention will be described.
  • the compound of the present invention can be suitably used for a thermal transfer recording sheet in order to improve the light resistance of a colored product.
  • the heat-sensitive transfer recording sheet according to the present invention comprises a substrate, and a color material layer formed by film-forming a composition containing the compound of the present invention on the substrate.
  • the color material layer has at least a yellow layer, a magenta layer and a cyan layer.
  • FIG. 2A shows an example of a thermal transfer recording sheet according to the present invention.
  • the thermal transfer recording sheet 200 shown in FIG. 2A has a base 230 and a color material layer 210 on the base 230.
  • the color material layer 210 has the yellow layer 211, the magenta layer 212, and the cyan layer 213 in the horizontal direction.
  • the thermal transfer recording sheet is heated by a heating means such as a thermal head in a state in which the color material layer of the thermal transfer recording sheet and the color material receiving layer provided on the surface of the image receiving sheet are superimposed. Heat using. By doing this, the color material in the color material layer of the heat-sensitive transfer recording sheet is transferred to the color material receiving layer of the image receiving sheet, thereby forming an image.
  • a heating means such as a thermal head
  • the coloring material layer contains a compound represented by the formula (1) or (2), a coloring material, a binder resin, a surfactant and a wax as needed, and a medium.
  • the method for producing the thermal transfer recording sheet of the present invention is not particularly limited, but in general, it can be obtained as follows.
  • the compound represented by the formula (1) or (2), the coloring material, the binder resin, and, if necessary, the surfactant and the wax are gradually added to the medium with stirring, and the medium is sufficiently blended.
  • the composition is stably dissolved or dispersed in the form of fine particles by applying mechanical shear force using a disperser to prepare a dispersion (ink).
  • the dispersion is applied to a base film as a substrate and dried to form a colorant layer.
  • the heat-sensitive transfer recording sheet of the present invention can be obtained by forming a transferable protective layer, a heat-resistant lubricating layer and the like described later, as necessary.
  • the thermal transfer recording sheet of the present invention is not limited to the thermal transfer recording sheet produced by the above-mentioned production method.
  • each component used for a color material layer is demonstrated in detail.
  • the coloring material As the coloring material, as the coloring material to be used for thermal transfer recording, the saturation of the coloring agent suitable for the present invention described above, ie, methine dyes, azomethine dyes, triphenylmethane dyes and the like High dyes are preferred. Furthermore, methine dyes and azomethine dyes are preferable. Among the above-mentioned dyes, dyes having sublimation are used in the thermal transfer recording sheet.
  • the colorants may be used alone or in combination of two or more.
  • the amount of the colorant used is 1 to 150 parts by mass with respect to 100 parts by mass of the binder resin contained in the colorant layer, and 50 to 120 parts by mass from the viewpoint of the dispersibility of the colorant in the dispersion.
  • the total amount is preferably within the above range.
  • the amount of the compound represented by the formula (1) or (2) is not particularly limited, but it is 0.1 part by mass to 100 parts by mass of the color material (total mass part of the color material). It can be used in the range of 100 parts by mass.
  • the range of 0.5 parts by mass to 50 parts by mass is preferable, and in particular, the range of 1.0 parts by mass to 30 parts by mass is more preferable.
  • the binder resin is not particularly limited, but water soluble resins such as cellulose resin, polyacrylic acid resin, starch resin, and epoxy resin; polyacrylate resin, polymethacrylate resin, polystyrene resin, polycarbonate resin, It is preferable that it is resin soluble in organic solvents, such as polyether sulfone resin, polyvinyl butyral resin, ethyl cellulose resin, acetyl cellulose resin, polyester resin, AS resin, and phenoxy resin. One of these resins may be used alone, or two or more of these resins may be used in combination as needed.
  • a surfactant may be added to the thermal transfer recording sheet of the present invention in order to have sufficient lubricity when heating with a thermal head (during printing).
  • Surfactants include cationic surfactants, anionic surfactants and nonionic surfactants.
  • Examples of the cationic surfactant include dodecyl ammonium chloride, dodecyl ammonium bromide, dodecyl trimethyl ammonium bromide, dodecyl pyridinium chloride, dodecyl pyridinium bromide and hexadecyl trimethyl ammonium bromide.
  • anionic surfactant examples include fatty acid soaps such as sodium stearate and sodium dodecanoate, sodium dodecyl sulfate, sodium dodecyl benzene sulfate and sodium lauryl sulfate.
  • nonionic surfactants include dodecyl polyoxyethylene ether, hexadecyl polyoxyethylene ether, nonylphenyl polyoxyethylene ether, lauryl polyoxyethylene ether, sorbitan monooleate polyoxyethylene ether, and monodecanoyl sucrose.
  • a wax may be added to the thermal transfer recording sheet of the present invention in order to provide sufficient lubricity when the thermal head is not heated.
  • Waxes that can be added include, but are not limited to, polyethylene wax, paraffin wax, fatty acid ester wax.
  • an ultraviolet absorber, preservative, antioxidant, antistatic agent, viscosity modifier and the like may be added to the thermal transfer recording sheet of the present invention as required.
  • the medium used to prepare the dispersion when forming the colorant layer is not particularly limited, and examples thereof include water and an organic solvent.
  • Organic solvents include alcohols such as methanol, ethanol, isopropanol and isobutanol; cellosolves such as methyl cellosolve and ethyl cellosolve; aromatic hydrocarbons such as toluene, xylene and chlorobenzene; esters such as ethyl acetate and butyl acetate Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; halogenated hydrocarbons such as methylene chloride, chloroform and trichloroethylene; ethers such as tetrahydrofuran and dioxane; N, N-dimethylformamide, N-methyl pyrrolidone is preferable .
  • the organic solvents may be used alone or in combination of two or more
  • the substrate is not particularly limited as long as it is a film that supports the color material layer and has a certain degree of heat resistance and strength, and known materials can be used.
  • polyethylene terephthalate films are preferable from the viewpoint of mechanical strength, solvent resistance and economy.
  • the thickness of the substrate is 0.5 to 50 ⁇ m, and preferably 3 to 10 ⁇ m from the viewpoint of transferability
  • the wettability, adhesion and the like of the coating liquid tend to be insufficient. Therefore, it is preferable to perform adhesion treatment on the surface (formation surface) of the base material on which the color material layer is to be formed, if necessary.
  • the color material layer may be formed on one side or both sides of the substrate.
  • the adhesion treatment is not particularly limited, and examples thereof include ozone treatment, corona discharge treatment, ultraviolet treatment, plasma treatment, low temperature plasma treatment, primer treatment, chemical treatment and the like. In addition, a plurality of these processes may be combined.
  • An adhesion layer may be coated on a substrate as adhesion processing of the above-mentioned substrate.
  • the adhesive layer is not particularly limited, but, for example, the following can be used. Fine particles of organic materials such as polyester resin, polystyrene resin, polyacrylic acid ester resin, polyamide resin, polyether resin, polyvinyl acetate resin, polyethylene resin, polypropylene resin, polyvinyl chloride resin, polyvinyl alcohol resin, polyvinyl butyral resin, Fine particles of inorganic materials such as silica, alumina, magnesium carbonate, magnesium oxide and titanium oxide.
  • the thermal transfer recording sheet of the present invention may contain the compound represented by the formula (1) or (2) in the protective layer.
  • FIG. 2B shows an example of a thermal transfer recording sheet according to the present invention.
  • the thermal transfer recording sheet 240 shown in FIG. 2B has a base 230, and a coloring material layer 210 and a protective layer 220 on the base 230.
  • the color material layer 210 has a yellow layer 211, a magenta layer 212, and a cyan layer 213 in a surface sequential manner. Further, the color material layer 210 and the protective layer 220 are also formed in a surface sequential manner.
  • the protective layer 220 contains the compound represented by Formula (1) or (2).
  • the protective layer contains a compound represented by the formula (1) or (2)
  • the protective layer comprises at least one compound selected from the group consisting of compounds represented by the formula (1) or (2). Including. Also when the compound represented by Formula (1) or (2) is contained in a protective layer, the same effect as the case where the compound represented by Formula (1) or (2) is contained in a color material layer is obtained. You can get it.
  • the binder resin used in the protective layer is not particularly limited, but is preferably the following.
  • Acrylic resins such as polystyrene, polymethyl methacrylate and polyethyl acrylate, styrene resins such as poly ⁇ -methylstyrene, polyvinyl chloride, polyvinyl acetate, vinyl chloride-vinyl acetate copolymer, polyvinyl butyral, polyvinyl acetal
  • synthetic resins such as vinyl resins such as polyamide resins, epoxy resins, polyurethane resins, petroleum resins, ionomers, ethylene-acrylic acid copolymers and ethylene-acrylic acid ester copolymers.
  • the amount of the compound represented by the formula (1) or (2) used in the present invention is preferably 0.1 to 50 parts by mass with respect to 100 parts by mass of the binder resin, and the color of the print and light resistance From the viewpoint of improving the properties, the content is more preferably 0.5 to 20 parts by mass.
  • the thickness of the layer is preferably about 0.1 ⁇ to 5 ⁇ .
  • the layer containing the compound an acrylic resin such as polymethyl methacrylate and polyethyl acrylate is included to facilitate peeling from the sheet, and the thickness is about 0.1 ⁇ to 1.5 ⁇ . It is more preferable to have a release layer.
  • the layer is configured on the above-mentioned base layer. Since the protective sheet for thermal transfer recording of the present invention contains the compound represented by the formula (1) or (2), it is possible to provide a thermal transfer recording sheet in which the light resistance of the colored material is improved.
  • the compounds of the present invention can be suitably used in toners in order to improve the light fastness of colored materials.
  • the toner of the present invention contains a compound represented by the formula (1) or (2), a colorant, a binder resin, and, if necessary, a magnetic material, a wax, a charge control agent, other additives, etc. Do.
  • the colorant as long as the colorant is generally used in the toner, one type may be used alone, or two or more types may be used in combination. Also, depending on the toner production method, it can be used in combination with a known pigment or dye in order to adjust the color tone and the like. In particular, the effects of the present invention are exhibited when a dye other than the pigment is used as the colorant of the toner.
  • an oil-based dye generally called a disperse dye or a sublimation dye can be suitably used.
  • the effects of the present invention are most exhibited when used in combination with dyes of high chroma, such as methine, azomethine and triphenylmethane.
  • the usage-amount of the compound represented by Formula (1) or (2) of this invention is not specifically limited, With respect to 100 mass parts (total mass part of coloring agents) of coloring agents used, It can be used in the range of 0.1 parts by mass to 100 parts by mass. The range of 0.5 parts by mass to 50 parts by mass is preferable, and in particular, the range of 1.0 parts by mass to 30 parts by mass is more preferable.
  • the compounds of the present invention are suitable for either pulverized toners or liquid developing toners.
  • a pulverized toner is obtained by melt-kneading a coloring agent and the like in a binder resin, finely pulverizing the kneaded product with a pulverizing apparatus, and classifying the finely pulverized product with a classifier to obtain toner particles having a desired particle size.
  • the toner for liquid development is obtained by dispersing or dissolving a coloring resin powder (toner) and, if necessary, an auxiliary agent such as a charge control agent and wax in an electrically insulating carrier liquid.
  • the color filter which has a resist layer containing the compound represented by Formula (1) or (2) is demonstrated.
  • the color filter for example, red, green, blue
  • the resist composition for color filters containing the compound of the invention and a colorant is used. By doing this, it is possible to obtain a color filter that is highly colored and excellent in light resistance.
  • each color coloring pixel is not specifically limited, For example, it can carry out by the inkjet method, the printing method, the photolithographic method etc.
  • an inkjet method When an inkjet method is used, a black matrix is formed on a glass substrate, and a color filter resist composition is sprayed as an ink on the opening of the black matrix using an inkjet device to color it, and heat treatment is performed. Form.
  • a water repellent such as silicon or fluorine can also be added to the black matrix.
  • a resist composition for a color filter is applied and dried.
  • the resist composition is applied on a transparent substrate so that the film thickness when dried is 0.1 to 20 ⁇ m, preferably 0.5 to 5 ⁇ m, and then dried.
  • the resist composition for a color filter of the present invention comprises a binder resin, a medium, a colorant and the compound of the present invention.
  • the binder resin and the medium those conventionally known can be used depending on the production method of the color filter used and the application.
  • the colorant is not particularly limited as long as it can be generally used in the color filter resist composition.
  • the effect of the present description is most exhibited when used in combination with the colorant suitable for the present invention described above, that is, dyes having high chroma such as methine type, azomethine type and triphenylmethane type.
  • the usage-amount of the compound represented by Formula (1) or (2) is not specifically limited, It is 0.1 with respect to 100 mass parts of coloring agents (total mass part of coloring agents) used. It can be used in the range of parts by mass to 100 parts by mass. The range of 0.5 parts by mass to 50 parts by mass is preferable, and in particular, the range of 1.0 parts by mass to 30 parts by mass is more preferable.
  • the analyzers include 1 H nuclear magnetic resonance spectroscopy ( 1 H-NMR) instruments (AVANCE-600 NMR spectrometer, manufactured by BRUKER), and high performance liquid chromatograph mass spectrometer (LCMS-2010, Shimadzu Corporation) Manufactured by Mfg. Co., Ltd., TG-DTA (STA 7200 RV, manufactured by Hitachi High-Tech Science Co., Ltd.) was used.
  • 1 H-NMR 1 H nuclear magnetic resonance spectroscopy
  • AVANCE-600 NMR spectrometer manufactured by BRUKER
  • LCMS-2010 high performance liquid chromatograph mass spectrometer
  • Preparation Example 1 Preparation of Compound (1-3) The following materials were added to a solution of N, N-dimethylphenylenediamine (A-1) (3.3 g, 24 mmol) in 20 mL of toluene and purged with nitrogen. Palladium acetate (0.5 g, 2.4 mmol) 2- (di-tert-dibutylphosphino) biphenyl (0.72 g, 2.4 mmol) Halide (B-4) (15.1 g, 53 mmol) Sodium tert butoxide (6.9 g, 72 mmol)
  • Preparation Examples 2 to 3 Preparation of Compounds (1-8) and (1-10) Preparation Example 1 was used except that (A-5) was used instead of the diamino compound (A-1) and (B-2) or (B-4) was used instead of the halide (B-4). Compounds (1-8) and (1-10) were produced in the same manner.
  • Production Example 4 to 6 Production of Compounds (2-3), (2-8), and (2-10) Compounds (2-3) and (2-8), in the same manner as in Preparation Examples 1 to 3, except that the amount of silver trifluoromethanesulfonate (I) used in Preparation Examples 1 to 3 was changed to 2 times. And (2-10) were produced.
  • Examples 1 to 8 and Comparative Examples 1 to 5 [Preparation of an image sample for evaluating the light resistance of a bar coat]
  • the liquid compositions (1) to (8) manufactured above and the comparative liquid compositions (1) to (5) were subjected to a bar coat method (bar number No. 10 of bar coater) to measure the hiding factor
  • the coating solution was applied to the solution and air-dried overnight to prepare an image sample for light resistance evaluation.
  • Evaluation criteria are as follows. A: 150 ⁇ lightfastness improvement (%) B: 101 ⁇ light resistance improvement (%) ⁇ 150 C: Improvement of light resistance (%) ⁇ 101 The obtained results are shown in Table 1. When the light resistance improvement (%) exceeded 101, the effect of the present invention was obtained, and when it exceeded 150, it was judged that the level at which the effect of the invention was sufficiently obtained.
  • the light resistance is excellent and the storage stability of the liquid composition is good.
  • Examples 9 to 16 and Comparative Examples 6 to 10 [Preparation of image sample for sublimation printing light resistance]
  • the liquid compositions (1) to (8) and the comparative liquid compositions (1) to (5) were formed of a polyethylene terephthalate film having a thickness of 4.5 ⁇ m (Lumirror (registered trademark); manufactured by Toray Industries, Inc.) It applied on top so that thickness after drying might be set to 1 micrometer, and it was made to dry.
  • the thermal transfer recording sheets (1) to (8) and the comparative thermal transfer recording sheets (1) to (5) were produced.
  • the thermal transfer recording sheets (1) to (8) and the comparative thermal transfer recording sheets (1) to (5) are transferred to printing paper using a modification of a photo printer SELPHY manufactured by Canon Inc. Image samples were prepared.
  • Evaluation criteria are as follows. A: 150 ⁇ lightfastness improvement (%) B: 101 ⁇ light resistance improvement (%) ⁇ 150 C: Improvement of light resistance (%) ⁇ 101 The obtained results are shown in Table 2. When the light resistance improvement (%) exceeded 101, the effect of the present invention was obtained, and when it exceeded 150, it was judged that the level at which the effect of the invention was sufficiently obtained.
  • Example 17 [Preparation of protective layer sheet] While stirring 3 parts of the compound (1-3) synthesized in Preparation Example 1 in 90 parts of a 1: 1 mixed solvent of methyl ethyl ketone and toluene, polyvinyl butyral resin (trade name: DENKA 3000-K, Electric Chemical Industry (stock 15 parts were added little by little to obtain a liquid composition (12).
  • the liquid composition (12) is dried to a thickness of 0.5 ⁇ m on the substrate using a polyethylene terephthalate film (Lumirror; Toray Industries, Inc.) with a thickness of 4.5 ⁇ m as the substrate. As it was applied and dried, a protective layer sheet was prepared.
  • Example 18 [Manufacture of toner] The toner was manufactured by the method described below.
  • Binder resin polyyester resin
  • glass transition temperature Tg 55 ° C.
  • acid value 20 mg KOH / g
  • hydroxyl value 16 mg KOH / g
  • main peak molecular weight Mp 4500
  • number average molecular weight Mn 2300
  • weight average molecular weight Mw 38000
  • Compound (1-8) 0.5 parts by mass
  • Solvent. Blue 5 0.5 parts by mass ⁇ 1,4-di-t-butyl salicylic acid aluminum compound: 0.5 parts by mass ⁇ Paraffin wax (maximum endothermic peak temperature 78 ° C.): 5 parts by mass
  • the above materials were well mixed using a Henschel mixer (trade name: Model FM-75J, manufactured by Mitsui Mining Co., Ltd.). Thereafter, the mixture was kneaded at a feed amount of 60 kg / hr by a twin-screw kneader (trade name: PCM-45 type, manufactured by Ikegai Iron Works Co., Ltd.) set to a temperature of 130 ° C. The temperature of the kneaded product at the time of discharge was about 150.degree.
  • the obtained kneaded product was cooled, coarsely crushed with a hammer mill, and then finely pulverized with a mechanical grinder (trade name: T-250, manufactured by Turbo Kogyo Co., Ltd.) at a feed amount of 20 kg / hr. Furthermore, toner particles were obtained by classifying the obtained finely pulverized product using a multi-division classifier utilizing the Coanda effect.
  • the obtained toner (1) has a weight average particle diameter (D4) of about 6.0 ⁇ m, particles having a particle diameter of 4.1 ⁇ m or less are 29.0% by number, and particles having a particle diameter of 10.1 ⁇ m or more are It was 0.8% by volume.
  • the toner (1) was fixed on a CLC color copy sheet (manufactured by Canon Inc.) using a modified LBP-5300 (trade name, manufactured by Canon Inc.) with a fixing image of 0.45 mg / cm 2 applied amount Was produced.
  • cyan O.D. after the light resistance test was compared with the image not containing the compound of the present invention with the same colorant composition. D. was 154%. By this, it was confirmed that it is excellent in light resistance by containing the compound of this invention.
  • Example 19 [Production of color filter]
  • the resist composition for color filters and the color filter were manufactured by the method described below.
  • Acrylic copolymer composition having a monomer ratio of 40% by mass of n-butyl methacrylate, 30% by mass of acrylic acid and 30% by mass of hydroxyethyl methacrylate (weight-average molecular weight Mw: 10,000) 6.7 parts of dipentaerythritol pentamer Acrylate 1.3 parts-2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone (photopolymerization initiator) 0.4 parts-cyclohexanone 96 parts Filtered with a 1.5 ⁇ m filter after stirring Thus, a resist composition for color filter (1) was obtained.
  • the color filter resist composition (1) was spin-coated on a glass substrate, dried at 90 ° C. for 3 minutes, exposed on the entire surface, and post cured at 180 ° C. to produce a color filter (1). .
  • cyan O.D. after the light resistance test was compared to a color filter having the same colorant composition and not containing the compound of the present invention. D. was 170%. That is, it was confirmed that the light resistance is excellent by containing the compound of the present invention.
  • the resist ink for a color filter (1) was changed to the compound (2-10) with the same composition as that of the ink for a resist composition (2), and the ink for a resist (2) using the comparative example compound (3) After storage for time, aggregates were observed in the resist ink (2). On the other hand, it was confirmed that the resist ink composition containing the compound of the present invention did not generate aggregates and the like, and was excellent in storage stability.
  • the compounds of the present invention are characterized in that they improve the light fastness of the color product. Moreover, the liquid composition containing the compound of this invention is excellent in storage stability.
  • the compound of the present invention can be suitably used to improve the light fastness of a colorant for a thermal transfer recording sheet excellent in light fastness, a toner and a resist composition for a color filter.

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  • Chemical & Material Sciences (AREA)
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  • General Physics & Mathematics (AREA)
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Abstract

L'invention concerne un composé et similaire ayant une excellente résistance à la lumière et une excellente stabilité au stockage. L'invention concerne également un composé caractérisé en ce qu'il présente une structure représentée par la formule (1) ou (2). [Dans les formules (1) et (2), R1 et R2 représentent chacun indépendamment un groupe alkyle non substitué en C1-8; R3 et R4 représentent chacun indépendamment un atome d'hydrogène, un groupe alkyle non substitué en C1-8 ou un groupe alkyle substitué, un groupe alcényle non substitué en C2-8 ou un groupe alcényle substitué, un groupe aralkyle non substitué en C7-12 ou un groupe aralkyle substitué, ou un groupe aryle non substitué en C6-12 ou un groupe aryle substitué, ou R3 et R4 se lient pour former un hétérocycle contenant de l'azote; R5 et R6 représentent chacun indépendamment un atome d'hydrogène, un groupe alkyle non substitué en C1-8 ou un groupe alkyle substitué, un groupe alcényle non substitué en C2-8 ou un groupe alcényle substitué, un groupe aralkyle non substitué en C7-12 ou un groupe aralkyle substitué, ou un groupe aryle non substitué en C6-12 ou un groupe aryle substitué, ou R5 et R6 se lient pour former un hétérocycle contenant de l'azote; les substituants dans les groupes alkyle substitués de R3-R6 sont des groupes cyano ou des groupes alcoxy (cependant, le nombre d'atomes de carbone dans les substituants n'est pas inclus dans le nombre d'atomes de carbone stipulés ci-dessus); les substituants dans les groupes alcényle substitués, les groupes aralkyle et les groupes aryles de R3-R6 sont des groupes fonctionnels choisis dans le groupe constitué par des groupes alkyles, des groupes cyano et des groupes alcoxy (cependant, le nombre d'atomes de carbone dans les substituants n'est pas inclus dans le nombre d'atomes de carbone stipulés ci-dessus); et X- représente un anion.]
PCT/JP2019/001367 2018-01-25 2019-01-18 Composé, composition liquide, feuille d'enregistrement par transfert thermique, toner, composition de réserve pour filtre coloré et filtre coloré WO2019146506A1 (fr)

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US11472962B2 (en) 2018-01-17 2022-10-18 Canon Kabushiki Kaisha Compound, ink, resist composition for color filter, sheet for heat-sensitive transfer recording, and toner
US11021436B2 (en) 2018-01-25 2021-06-01 Canon Kabushiki Kaisha Compound, liquid composition, thermal transfer recording sheet, toner, resist composition for color filter, and color filter
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